6-aminohexyl 2-acetamido-2-deoxy-β-D-galactopyranoside | 110101-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-aminohexyl 2-acetamido-2-deoxy-β-D-galactopyranoside
• 英文别名: N-acetyl-D-galactosamine；6-aminohexyl β-N-acetylgalactosamine；6-Aminohexyl 2-acetamido-2-deoxy-beta-d-galactopyranoside；N-[(2R,3R,4R,5R,6R)-2-(6-aminohexoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 110101-40-1
• 化学式: C₁₄H₂₈N₂O₆
• 分子量: 320.386
• InChiKey: BYQGHEVGCGGHPF-RKQHYHRCSA-N

物化性质

• 沸点：
  593.6±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  134
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-aminohexyl 2-acetamido-2-deoxy-β-D-galactopyranoside 在 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 G-ah-GalNAc
  参考文献：
  名称：

  New and more efficient multivalent glyco-ligands for asialoglycoprotein receptor of mammalian hepatocytes

  摘要：

  New multi-valent, carbohydrate ligands that contain terminal N-acetylgalactosamine (GalNAc) or lactose (Lac) were prepared using a nitrilotriacetic acid (NTA) derivative of L-lysine as scaffold. Tri-valent structures were prepared by attaching an x-amino glycoside of GalNAc or Lac to each of the three carboxyl groups of N-epsilon-protected N-alpha-dicarboxymethyl-L-lysine. In addition, a hexa-valent lactoside was synthesized by attaching N-epsilon-deprotected trivalent lactoside to each of the carboxyl group of N-alpha-(trifluoroacetamido) hexanoyl L-aspartic acid. Tri-valent GalNAc glycosides and the hexa-valent lactoside had high affinity (dissociation constants approaching nM) for rat hepatocytes. The hexa-valent lactoside, after de-Ne-protection, was modified with a chelator, diethylenetriaminepentaacetic acid (DTPA), through which a fluorescent or radioactive tag, such as europium or indium, can be firmly attached. Intravenous infusion of (111)Indium-tagged hexa-valent lactoside to rats and mice resulted in nearly exclusive accumulation of radioactivity in the liver.(C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.027
• 作为产物：
  描述：

  6-溴正己醇 在 palladium on activated charcoal sodium azide 、 三氟甲磺酸三甲基硅酯 、 氢气 、 溶剂黄146 、 甲胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-aminohexyl 2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  一种新的同双功能对硝基苯基酯偶联剂，用于制备新糖蛋白。

  摘要：

  已经设计了新的接头系统并将其应用于新糖蛋白合成。寡糖ω-氨基烷基糖苷与同双功能的己二酸对硝基苯基二酯在干燥的DMF中反应，可得到相应的酰胺半酯，收率高，稳定性好，可进行色谱纯化。随后在非常温和的条件下与牛血清白蛋白结合，可以有效地提供相应的新糖蛋白。该方法非常适合于极少量（mg）的寡糖和蛋白质的偶联。[结构：见文字]

  DOI：

  10.1021/ol048614m

文献信息

• NOVEL LIVER-TARGETING AGENTS AND THEIR SYNTHESIS
  申请人：LEE REIKO TAKASAKA

  公开号：US20110077386A1

  公开（公告）日：2011-03-31

  This invention provides novel liver targeting agents and their synthetic methods. A liver targeting agent, with a lysine based nitrilo triacetic acid structure as backbone which acquires multivalency with saccharide groups, to bind with a galactosamine chain or lactose chain is disclosed. In particular, only one amino acid L-lysine is involved to provide trivalency. All carboxyl groups in N ε -benzyloxycarbonyl-N α -dicarboxymethyl-L-lysine can be conjugated with three glycosides of ahGalNAc or ahLac in one step. This invention also provides a hexa-lactoside. In particular, the TFA-AHA-Asp was used to conjugate 2 moles of NTA(ahLac) 3 . This invention also provides a method for adding a spacer between NTA and DTPA. The extended hepatocyte-specific glyco-ligand has higher 111 In-radiolabelling yield than those non-extended.

  该发明提供了新型的肝靶向药物及其合成方法。一种肝靶向药物，以赖氨酸为骨架，具有氨基三乙酸结构，通过与糖苷基团形成多价性，与半乳糖胺链或乳糖链结合。具体来说，仅涉及一种氨基酸L-赖氨酸，以提供三价性。Nε-苄氧羰基-Nα-二羧甲基-L-赖氨酸中的所有羧基可以在一步中与三个ahGalNAc或ahLac的糖苷结合。该发明还提供了一种六乳糖苷。具体来说，TFA-AHA-Asp被用于将2摩尔的NTA(ahLac)3结合。该发明还提供了一种在NTA和DTPA之间添加间隔物的方法。扩展的肝细胞特异性糖基配体的111In标记产率高于非扩展的配体。